How to Date Successfully as a SHY Executive

Every day I have executives that come in for executive coaching on a workplace issue, or relationship management issues that need help with communication and scripting important conversations.

Time and time again, I hear,

“I know I came to you for this business advice but would you mind giving me some dating advice.

I have a relationship issue. Would you mind helping me find the right words for online dating?”

This is one of the most important work-life balance issues because when it comes to matters of the heart—it’s hard to focus on the job when you’ve got dating issues or relationship issues. Research shows that when we are not happy in our personal relationships it affects us in all areas of our lives.

For these reason it is a top-tier work-life balance issue.

This is especially true if you have found yourself single after many years of marriage which ended in divorce or the loss of your spouse. Or, if you have spent many years focusing on your career and haven’t really felt successful finding someone to love and you want to finally take this part of your life seriously and find a mate.

You might want to date but there can be such a contrast between the self-mastery you feel professionally on the job and the insecurity, shyness, and even timidity that takes over when you try to date. If this sounds like you, you may feel lonely and want to have someone special in your life but feel exhausted and intimidated by the entire process.

It’s especially tough when you spend so much of your time in the powerhouse part of yourself on the job. You may have a very busy, professional career where you feel tired after long days of work, possibly managing people, running a company or just making a living.

And then, after all that, you are supposed to come home and sit at the computer, which you may have spent all day glaring at and find the right words in your search—or try to find those things which require you to tap into the most vulnerable parts of yourself.

On the outside you may be an accomplished professional but on the inside you can feel like that shy little girl who was too afraid to talk to the boy at the water cooler. Dating takes a different set of skills, it makes you feel insecure and you may lack the self-confidence you need to succeed.

You should know you’re not alone.

Many high powered executive types just like you struggle to find the same success they have at work in dating. Here are lessons learned from executives that I’ve worked with that are just like you.

Get to know yourself ~ self-reflection is key

Sometimes it takes a while to understand our own part in why we haven’t been able to find someone to love. Darla was a senior VP and a busy executive managing 200 employees. She was completely frustrated by dealing with the two sides of herself. The powerhouse Vs. nervous dater.

She was also completely unaware of the things she was saying that were causing date after date to crash. She only knew that she was completely beaten up by years of online dating and thought there were no compatible men out there. Her heart was broken after repeated failures with online dating. She was a beautiful brunette with straight black hair, 130 pounds, head of a sales department for a very successful start-up.

Together, step-by-step, we broke down her communication on these dates to figure out if there was anything she was saying and doing that might be sending the wrong message. It didn’t take long before the subtle body language cues and conflicting verbal messages began to reveal themselves.

She had an interview style for her first dates. At work she was used to dropping her chin, lowering her voice and cutting to the chase when interviewing new people. What she didn’t realize was that she had learned from her early days on the job to overcome her shyness with authoritative voice and strong body language. She didn’t want anyone to “see her vulnerabilities or the shyness she had struggled with her entire life”. This made her seem intimidating to dating prospects.

The problem with her approach was that she didn’t feel like much fun. She began to realize that she was bringing her corporate mask to her dates. This was her armored-self that she had developed after painful years of anxiety trying to hide her shyness while she stood up for herself at work.

But this wasn’t her true self.

Her true self was fun-loving and loved to dance. She had to feel comfortable for her humor, quick wit, candor and the colors of her personality to come out. She knew she had all these qualities inside. Her shyness had been preventing her from showing what made her attractive to prospects.

Text Dating can get a little tricky

Text dating can be especially painful when you are shy. This can be especially true if you are not a big texter. If you are shy you may have trouble formulating your words when you are trying to impress a love interest. The added stress of sounding engaging in a few words without seeming too needy or too eager can be a real challenge.

You may even be accidentally sabotaging your efforts without even realizing it due to your shyness: it may feel so unnatural that you are sending the message that you are not interested when quite the opposite is true. It’s important to learn about the things you are doing or saying that are getting in the way of having the love you want.

When Jim went over his text message chain between him and his love interest with me, he had no idea that even though he was crazy about this girl, his text messages sounded cool and aloof, and he missed obvious overtures she was making to take their connection to a deeper level.

They texted for months until one day she dropped off. She lost interest over time and met someone else because she thought he wasn’t interested in her and only wanted to be her friend. He was heartbroken.

If all of this sounds painfully like you, it’s important to take steps to help you overcome your fears, and face your shyness so you can succeed at the dating game and have the love you deserve.

Don’t go it alone

If you are already shy, doing something by yourself only adds to the anxiety. You may need to find the support to help you step outside of your comfort zone, so you don’t miss overtures. Support can also help you say the right words to bring your love interest close.

One man, a divorced, high-powered attorney said to me, “I spend all day in the courtroom and am a force to be reckoned with in that world. And yet, I sat next to a lovely woman in her 40’s at the coffee shop who was obviously flirting with me -- I looked away hiding behind my newspaper. I felt like the shy kid I was growing up. I couldn’t find my words. The problem is that I am 49! After a while, I was so frustrated with myself that I got up and left. Now I am mad that I missed that opportunity.”

The feeling we feel when we are attracted to someone can completely overwhelm our abilities to communicate and say the right words, especially when shyness takes over.

This is the reason why after over 25 years of working with clients I have noticed that single people who are attracted to each other don’t always end up dating— Especially when we’re got full and busy lives that are distracting—or you get so used to being rejected that you expect it. Prospects that could have made a good relationship together don’t always end up together because the voices inside your head can cause you to give up way too soon.

You may lack the communication skills to make it happen or get through the rough patches, or even say the right things to help their love interest draw closer. We get coaching in everything else we do from brushing our teeth to using our new phones and yet, when it comes to the most important parts of our lives, our relationships, we tend to get no coaching at all. Here are some coaching tips to help you succeed.

Tips for the Shy Executive dating

Take a few minutes to deep breath and relax. Tell yourself everything will be ok.

Imagine taking off your corporate mask and setting it to the side. Remember this is not a corporate job interview.

Take it easy, give the other person a chance to relax too.

Authenticity helps. One man said, “This is hard for me. I have always been painfully shy.” She appreciated his honesty. They ended up together.

Asking questions of your love interest and reflecting on their answers can give you much-needed time to get comfortable.

Try to meet somewhere like an art museum where you can walk around and talk about different interesting things. Sometimes just dinner or drinks is too much pressure on both sides.

Don’t look for your type. Instead look for someone who “gets you” and whom you “get.” S/he may look very different than your type. Research shows that it is not the pedigree that is important when finding a mate, it is “getting each other.”

Most importantly, realize it is never too late to find love. But it may mean you need to give it the kind of focus

you would give to finding a new job. Just putting it on the back burner and telling yourself, “someday my love will come,” isn’t enough. This is a work-life balance issue that will enhance your fulfillment on the job as well. Why? Because when we are happy at home it makes for happier executives.

Donna LeBlanc and TherapySites expressly disclaim all warranties and responsibilities of any kind, whether express or implied, for the accuracy or reliability of the content of any information contained in this site, and for the suitability, results, effectiveness or fitness for any particular purpose of the content. You are solely responsible for your use or reliance on such information and any foreseeable or unforeseeable consequences arising out of such use or reliance. In no event will Donna LeBlanc or TherapySites be liable for any damages resulting from the use of or inability to use, the content, whether based on warranty, contract, tort or other legal theory, and whether or not Donna LeBlanc or TherapySites is advised of the possibility of such damages. In no event will Donna LeBlanc's and TherapySites's aggregate liability exceed U.S. $100.